8-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-5-carbamimidamidopentanamido]-12H-10-oxa-5-azatetraphen-12-iminium chloride

• ChemBase ID: 106591
• Molecular Formular: C39H39ClN8O5
• Molecular Mass: 735.23056
• Monoisotopic Mass: 734.27319407
• SMILES: NC(=N)NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)Nc1cc2oc3c(nc2cc1)c1c(c(=[NH2+])c3)cccc1.[Cl-]
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc1c(n2)c2ccccc2c(=[NH2+])c1)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1.[Cl-]
• InChI: InChI=1S/C39H38N8O5.ClH/c40-29-22-34-35(28-15-8-7-14-27(28)29)45-30-18-17-26(21-33(30)52-34)44-36(48)31(16-9-19-43-38(41)42)46-37(49)32(20-24-10-3-1-4-11-24)47-39(50)51-23-25-12-5-2-6-13-25;/h1-8,10-15,17-18,21-22,31-32,40H,9,16,19-20,23H2,(H,44,48)(H,46,49)(H,47,50)(H4,41,42,43);1H/t31-,32-;/m0./s1
• InChIKey: OYFTWBCLFJOXSP-UEMXOEKYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-5-carbamimidamidopentanamido]-12H-10-oxa-5-azatetraphen-12-iminium chloride
• IUPAC Traditional name: 8-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-5-carbamimidamidopentanamido]-10-oxa-5-azatetraphen-12-iminium chloride
• Synonyms: Z-Phe-Arg-MR; Z-FR-MR; Z-Phe-Arg-MR

Database IDs

• PubChem SID: 162105539
• PubChem CID: 25108746

CALCULATED PROPERTIES

• Acid pKa: 12.251651
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): 0.4843542
• LogD (pH = 7.4): 1.7573887
• Log P: 3.8854713
• Molar Refractivity: 222.1089 cm^3
• Polarizability: 74.707794 Å^3
• Polar Surface Area: 205.61 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MR052

A fluorogenic substrate for Cathepsin B
(Patent# 6,235,493-May 22, 2001)

REFERENCES

• Van Noorden, C.J.F. et al., Anal. Biochem. 252: 71 (1997).
• Boonacker, E. et al., J. Histochem. Cytochem 49: 1473 (2001).